After Lupe Fiasco's debut Food & Liquor suffered the "leak heard 'round the world" in 2006, leading to less-than-stellar album sales, the man born Wasalu Jaco had to come back in a major way. He did just that with "Superstar," the first single off his second album, The Cool. Laughing in the face of the sophomore slump, this Matthew Santos–assisted smash helped Lu attain superstar (get it?) status and pushed The Cool to gold status. The single peaked at No. 10 on the Billboard Hot 100 and ushered Fresh Cool Young Lu into hip-hop's A-list category.
#14. Lupe Fiasco f/ Matthew Santos "Superstar"